Dyestuffs and process of making same



Patented Feb. 9, 1926'.

T'EN T ounce.)

WILLIAM PABNELL BATE 8, F KEMIPTON, NORTH DAKOTA.

mrns'rurrs AND rnoc nss or name sum.

Ho Drawing.

To all whom it may concern;

Be it known that I, WILLIAM P. BA'ms, a citizen of the United States of Amerlca, and resident of Kempton, in the county of Grand Forks and State of North Dakota,

have invented certain new and useful Im- Ipiovements in Dyestufis and Processes of aking Same, of which the following is a.

specification. a

The present inventlon relates to a novel intermediate, and to a series of dyestuffs derivable from said intermediate. The mvention also embraces a process of rod ucing said intermediate; known to c emlsts as a chromogen.

In the preferred form of carrying out the process, aniline is diazotlzed at a temperature below 5 C., in known manner, the diazonium chloride thus formed is run 1nt o Application and August 25, 1924. Serial No. 734,085.

heating is continued until no further action is noticed, for one half to one hour).

The to uct formed melts and rises to the sur ace and can be separated by skimming.

Assuming is being used, the reaction may be expressed as follows: a

This compound is the chromogen 'corre-' sponding to the particular diamine above 40 mentioned. As stated before if the temperature is much below 90 0., the above body has beenshown by experiment not to be formed,in any commercial quant1t1es.'

This product, as will beseen, 1s a qumone hydrochloride, united by to an amino benzene. The above numbering of the positions is arbitrary, and for explanation.

The hydrogen and chlorine 1n position 1 are readily replaceable by various atoms or 5 groups, say COOH, --HSO, and many others, including both alkyl and aryl groups, forming dyesof various colors and shades. The NH in the II position reacts with various organic and inorganic acids, to

either confer solubility, or form dyes.

If positions I, and II are filled, the other hydrogens' on the rings are replaceable.

The chromogen (intermediate) itself is a dyestufl'; it dyes white feathers to produce an imitation of the Chinese wood duck feather but is improved by the addition of an OCH group, as in Example 1.

This body (the chromogen from m-phenylene diamine) is a dark blue green crystallin'e mass, insoluble inwater, ether, benzene, chloroform, etc. somewhat soluble in oils and fats.

It dyes feathers, fur, hair, etc. brown.

A series of dyes may be produced by a more or less direct substitution of the chlorine in position 1, by aliphatic or aro matic radicals, the products will be useful dyestuffs giving various colors from bright orange to brown, depending on the radical so substituted.

Ewmnple 1.A simple example consists in the reaction of the chromogen with an that meta phenylene diamine soluble in alcohol, almost entirely 7 iaquimolecular proportion of sodium methyate.

-H QOH;

+mocn, +N.c1 o1 n This roduct dyes white or light gray wild dudlr feathers to a peculiar brown,.an almost perfect imitation of the Chinese wood duck.

moo

n u+ on M E This on further treatment with fused zinc chloride, ives (by removal of one molecule of H,

This d eswool, even from a cold solution, to a brig 't orange.

Exam Ze 3.By substituting ara-hydroxy-p enyllycocoll in place of t e chlorine, a colored body dyeing a rich yellow (with a slight orange cast) is formed.

DQ iO E wample 4.The substitution of COOH in place of the chlorine. A thin paste'is made of the base with alcohol and water. A slight excess over one molecular equivalent of KCN is added, and the mixture heated for several hours on a water bath, thus forming the nitrile;

on This is further heated with somewhat dilute mineral acid, say 3 parts sulphuric to 2 parts of water, to hydrolyze the mtrile glvcoon This gives a deeper yellow than does Exam lei 0 number of products are formed by d1- rect sulfonation of the base, one believed to contain the grouping o o I o o was found to dye silk a rich golden brown 1 cal. This product (the oxymethyl This re resents a very simple substitu tion for t e chlorine, of an oxy l radiseems to be the most satisfactory of this series of to dye silk a rich yellow somewhat deeper than canary).

In cases where the chlorine is replaced by a radical (aromatic or aliphatic) and an NH, group is resent on the second rin the derivative ecpmes solublein an aci bath as is necessary 1n dyestuffs.

Where the position 1 and the free bonds of 1 the NH group are occupied b substituted or added radicals the other by rogen atoms of the rings are replaceable.

I have referred particularly to the use of diamines to unite with the diazonium chloride. It is also possible to em loy mono-amines in a similar manner. bus

with aniline there has been formed:

Cl h

This body can be used in the above reactions, with the' production of dyes of generally similar character to the above. If

one wishes the NH group present he would use the diamine, or one might use a monoamine with some other radical or group onthe ring.

As stated above, the reaction to form the base, 'or chromog'en, must be effected hot.

I claim:

1. A group of new bodies having the general formula I: O CX in which a: is a monovalent element or group.

2. A group of new bodies having the general formula QECX in which a: is a monovalent element or group.

3. A group of new bodies having the general formula in which R is any aromatic radical and m is a monovalent element or group.

4. A process which comprises addinga diazonium compound to an aromatic amine WILLIAM PARNELL BATES. 

